[6] Simmons served in the United States Army Reserve as a Military Intelligence Officer from 1969 to 2003, retiring at the rank of full colonel.

[6] Simmons joined the Central Intelligence Agency in 1969, working as an Operations Officer for a decade, including five years on assignment overseas in East Asia.

He ran the Phu Yen Province Interrogation Center from November 1970 to June 1972, according to an article by Douglas Valentine in Everything You Know is Wrong, and he "mounted numerous paramilitary and psychological warfare operations against" the Viet Cong.

In 1991, he became a member of the Connecticut House of Representatives, replacing incumbent Frank Turek who died in office.

Simmons led the successful fight to save the base and the BRAC removed it from its closure list on August 24, 2005.

Simmons also served on the House Homeland Security Committee as chairman of the Subcommittee on Intelligence, Information Sharing, and Terrorism Risk Assessment.

Simmons also championed Open Source Intelligence (OSINT) on Capital Hill, where he helped to legally define open source intelligence in the 2006 National Defense Authorization Act, requiring the Department of Defense to establish an OSINT program.

[17] As Simmons fared far better than other defeated Republican incumbents it was speculated he would try for a political comeback in 2008, which he did not rule out in conceding the 2006 election to Courtney.

[citation needed] On February 26, 2007, Simmons was nominated by Connecticut Governor M. Jodi Rell to become the State's first Business Advocate.

[22] Sen. Chris Dodd however announced in January 2010 that he would not be seeking re-election to the U.S. Senate due to high pressure from the Democratic Party leaders, falling poll numbers, and controversy over business dealings with Countrywide Financial.

While Simmons originally led in the polls early on, Linda McMahon gained traction on him in the primary and won at the Republican convention.

In late July – two weeks before the primary – however, he re-entered the race by airing TV ads, participating in debates, and accepting interviews with editorial boards.

On the Lee Elcee Show radio program, Simmons reflected on how Maynard had introduced his daughter and her husband.